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Check availability on Montegrossi Hotels with Pool

Tonight
26 Oct - 27 Oct
Tomorrow
27 Oct - 28 Oct
This weekend
30 Oct - 1 Nov
Next weekend
6 Nov - 8 Nov

Our top choices for Montegrossi hotels with a pool

An outdoor dining area with a table set for two, overlooking a pool and vineyard.
A villa with a swimming pool, outdoor seating, and a garden.
An outdoor dining area with a pool, potted plants, and umbrellas.
A restaurant with a table set for two, overlooking a scenic landscape.

1. Relais Vignale & Spa

Relais Vignale & Spa
Radda in Chianti
  • Discover a seasonal rooftop sanctuary with dual pools, poolside bar service, and stunning vineyard views in historic wine country.
฿5,831
฿7,575 total
includes taxes & fees
28 Oct - 29 Oct
Relais Vignale & Spa
A swimming pool with a stone deck, surrounded by trees and a castle-like building in the background.
A sunlit patio with a glass roof, stone walls, and outdoor seating.
An outdoor dining area with stone buildings and a tower, illuminated by ambient lighting.
A stone building with a garden, tall trees, and a clear blue sky.

2. Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World
Gaiole in Chianti
  • Serene pools with vineyard views offer both indoor and outdoor aquatic escapes.
฿11,140
฿12,633 total
includes taxes & fees
30 Oct - 31 Oct
Castello di Spaltenna- Small Luxury Hotels of the World
A woman in a blue bikini in a spa pool with a stone wall and a blue light fixture.
A narrow street with buildings on either side, a flag, and a bench.
A room with a view of a valley, a stone shelf with flowers, a wooden bench, and a fireplace.
A couple dining at an outdoor table with a view of the countryside.

3. Palazzo Leopoldo Dimora Storica & Spa

Palazzo Leopoldo Dimora Storica & Spa
Radda in Chianti
  • Sun-kissed pools in tuscan splendour beckon with historic charm and breathtaking views.
฿3,504
฿4,081 total
includes taxes & fees
23 Nov - 24 Nov
Palazzo Leopoldo Dimora Storica & Spa
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a clear sky.
A cozy living room with a sofa, a coffee table, and a view of greenery through large windows.
A narrow, tree-lined road leading to a house with a tiled roof and a stone wall on one side.
A building with a stone facade, a central arched doorway, and a window with a decorative frame.

4. Dievole Wine Resort

Dievole Wine Resort
Castelnuovo Berardenga
  • Splash into luxury at a Tuscan wine resort with two outdoor pools and vineyard views.
฿9,191
฿10,412 total
includes taxes & fees
16 Nov - 17 Nov
Dievole Wine Resort
A poolside area with lounge chairs and umbrellas, surrounded by stone flooring and greenery.
A bedroom with a large bed, wooden beams, stone wall, and a stone fireplace.
A stone-walled room with a table set for breakfast, featuring pastries, fruits, and a coffee station.
An outdoor dining area with stone walls, tables, and chairs, surrounded by greenery and a stone building in the background.

5. Ultimo Mulino Wellness Country Hotel

Ultimo Mulino Wellness Country Hotel
Gaiole in Chianti
  • Tuscan retreat offers sparkling outdoor pool with free cabanas, loungers, and refreshing poolside bar service.
฿3,706
฿4,379 total
includes taxes & fees
27 Oct - 28 Oct
Ultimo Mulino Wellness Country Hotel
A landscaped garden with a swimming pool, a vineyard in the background, and a stone pathway.
An aerial view of a property with a swimming pool, a sun terrace, and a vineyard in the background.
A spa area with stone flooring, wooden chairs, a table with amenities, and a view of a garden through a glass door.
A stone pillar with carvings, a glass door leading outside, and a person sitting on a lounge chair.

6. Hotel Villa Campomaggio

Hotel Villa Campomaggio
Radda in Chianti
  • Soak in mountain views from the sun-drenched outdoor pool at this Tuscan retreat where spa treatments and regional cuisine await.
฿5,570
฿6,354 total
includes taxes & fees
27 Oct - 28 Oct
Hotel Villa Campomaggio
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and hills.
An outdoor dining area with stone walls, tables, chairs, and umbrellas.
A modern living room with a white sofa, armchairs, and a coffee table.
A dining area with a table and chairs, a view of a landscape through an arched window, and a large umbrella providing shade.

7. Chapter Chianti, a Member of Design Hotels

Chapter Chianti, a Member of Design Hotels
Cavriglia
฿9,077
฿10,212 total
includes taxes & fees
27 Oct - 28 Oct
Chapter Chianti, a Member of Design Hotels
A pool area with lounge chairs and umbrellas, a large building in the background, and a view of the countryside.
A spacious living room with a high ceiling, exposed wooden beams, and a large arched brick structure. There are multiple seating areas with floral-patterned sofas and armchairs. A fireplace and bookshelves are visible in the background.
A table set for breakfast with various dishes, drinks, and a newspaper.
A large, historic building with a tiled roof and multiple windows, surrounded by lush gardens and a stone pathway.

8. Hotel Le Fontanelle

Hotel Le Fontanelle
Castelnuovo Berardenga
  • Dive into tranquil luxury at this hotel's indoor and seasonal outdoor pools, complemented by a poolside bar and loungers.
฿21,786
฿24,342 total
includes taxes & fees
27 Oct - 28 Oct
Hotel Le Fontanelle
A pool area with a stone wall, a wooden bridge, and a castle-like structure in the background.
A historic stone building with a large arched window and a small balcony.
A stone building with a tower, surrounded by people dining at tables with candles.
A rustic stone building with a wooden pergola, outdoor seating, and a garden with various plants.

9. Castello di Tornano Wine Resort

Castello di Tornano Wine Resort
Gaiole in Chianti
  • Poolside bliss awaits at this Tuscan wine resort where medieval castle meets vineyard views.
฿5,133
฿5,949 total
includes taxes & fees
27 Oct - 28 Oct
Castello di Tornano Wine Resort
A pool with a stone wall and a tree, surrounded by a clear sky and distant mountains.
An open door leading to a balcony with a table, chairs, and a vase of flowers.
A stone wall, a pink building, and a pool with a garden.
Room

10. Villa Barberino

Villa Barberino
Meleto
฿5,487
฿6,035 total
includes taxes & fees
27 Oct - 28 Oct
Villa Barberino
View all properties

Choose what matters most at hotels with a pool in Montegrossi

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Montegrossi Hotel Reviews

Hotel Borgo San Luigi

Hotel Borgo San Luigi

10/10 Excellent
"Borgo San Luis is a luxury destination! The four of us were treated as honored guests of great renown. The grounds were wide, varied, and immaculate. The breakfasts were special events for us foodies, and the swimming pool was refreshing even in October!. Parking was free, secure, and accessible. We easily saw why the Borgo was a destination for the weddings, feasts, and meetings that were taking place at the time of our visit -- but they were never intrusive. The staff were multi-lingual and honestly could not do enough for us. Should you ever desire a dream from which that you did not want to awaken, visit Borgo San Luis."
John 2-night trip
Posted 13 hours ago
Hotel Borgo San Luigi
Hotel Athena

Hotel Athena

10/10 Excellent
"Over all a good hotel in a good location, a little dated but clean and breakfast good"
Suzanne 2-night trip
Posted 17 hours ago
Hotel Athena
Hotel Italia

Hotel Italia

10/10 Excellent
"We stayed at this basic but nice 3-star hotel just one night while visiting Siena. We had a room for 3 for my wife and I and our adult daughter. The hotel was easy walking distance from the train/bus station. It's kind of weird because you enter an indoor shopping area across the street from the station and then go up about 6 banks of escalators to get up the hillside. Then the hotel is just a block away. One of the AC units didn't work but friendly staff helped start the other one. All staff were very friendly and spoke English. Easy walk a few blocks into the old city. Wonderful breakfast!!! We were able to leave our bags for most of the day while we explored the city prior to leaving on the bus again. I would definitely stay again."
Kurt 1-night trip
Posted 5 days ago
Hotel Italia
Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World

10/10 Excellent
"Beautiful quaint 1000 year old monastery turned into a hotel! The staff was extremely accommodating and we really enjoyed our stay. Very easy to get around all of Tuscany from this hotel."
Michelle 3-night trip
Posted 2 weeks ago
Castello di Spaltenna- Small Luxury Hotels of the World

Frequently asked questions

What are some hotels with pools in Montegrossi?
La Certosa di Pontignano: Offers a children's pool, a seasonal outdoor pool and a rooftop terrace. Hotel Athena: Features a rooftop terrace, an outdoor pool and a snack bar/deli. Hotel Executive: Features an indoor pool, an outdoor pool and 2 restaurants. NH Siena: Provides 2 restaurants, 2 outdoor swimming pools and a full-service spa. Hotel Chiusarelli: Hotel located near Piazza del Campo. Features a children's pool, a seasonal outdoor pool and free self parking.
What is there to see and do in Montegrossi?
Make a point to visit attractions such as Borgo di Vescine - Tenute di Castelvecchi and Chianti Observatory. During your stay, visit sights such as Badia a Coltibuono, Meleto Castle and Cantalici Winery.
When is the best time to book a hotel with a pool in Montegrossi?
You may want to consider a place to stay with an outdoor swimming pool if you'll be visiting Montegrossi in the warmest months of August, July or June, when the average temp is 22°C. Accommodation with an indoor pool may be the way to go if you are visiting during the coldest months of January, February or December, when the average temp is 6°C.

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